When I run tcmdump on the bastion, I see that it tries to connect to the
windows host but does not get any response.
When I try to directly connect to the windows machine using psrp it works
just fine.

On Thu, Sep 13, 2018 at 10:38 AM, Gil Shinar <[email protected]> wrote:

> Actually the error is a bit different:
> *ConnectTimeout: SOCKSHTTPConnectionPool(host='<windows host IP>',
> port=5985): Max retries exceeded with url: /wsman (Caused by
> ConnectTimeoutError(<urllib3.contrib.socks.SOCKSConnection object at
> 0x7f2a7d269450>, 'Connection to <windows host IP> timed out. (connect
> timeout=30)'))*
>
> On Thu, Sep 13, 2018 at 10:27 AM, Gil Shinar <[email protected]> wrote:
>
>> Hi Jordan,
>>
>> First thanks a lot for the detailed description!
>> I have tried the sock example but for some reason it does not work for me.
>> I configured the inventory as you have suggested (changed user and pass),
>> installed socks package (had some issues with pip but made it work with
>> system pip), in a different terminal connected to my bastion (had to use -i
>> <path to pem>) and run the ansible command. Not sure were it fails:
>> *ConnectionError: SOCKSHTTPConnectionPool(host='<windows host IP>',
>> port=5985): Max retries exceeded with url: /wsman (Caused by
>> NewConnectionError('<urllib3.contrib.socks.SOCKSConnection object at
>> 0x7f494a320450>: Failed to establish a new connection: [Errno 111]
>> Connection refused',))*
>>
>> Any help would be appreciated
>>
>> Thanks
>> Gil
>>
>> On Wednesday, September 12, 2018 at 7:06:35 PM UTC+3, Gil Shinar wrote:
>>>
>>> I have installed ansible 2.7 rc1 because I need a way to install stuff
>>> on  a windows machine via Linux server as a tunnel.
>>> After reading and trial and error, I have realized that it cannot be
>>> done using WinRM but only using psrp with ansible 2.7.
>>> I'm not sure what should be configured in the ansible_psrp_proxy parameter
>>> and how can ansible know that the tunnel is server is a Linux one that
>>> needs to connect using ssh.
>>> I have tried to configure the ansible.cfg to read a ssh.cfg file with
>>> the following content:
>>> Host <windows machine IP>
>>>   ProxyCommand ssh -W %h:%p ec2-user@<Linux server IP>
>>>   IdentityFile <path to pem file>
>>>
>>> Host bastion
>>>   Hostname <Linux server IP>
>>>   User ec2-user
>>>   IdentityFile <path to pem file>
>>>   ForwardAgent yes
>>>   ControlMaster auto
>>>   ControlPath ~/.ssh/ansible-%r@%h:%p
>>>   ControlPersist 5m
>>>
>>> Error message looks like that:
>>> ConnectTimeout: HTTPSConnectionPool(host='<windows machine IP>',
>>> port=5986): Max retries exceeded with url: /wsman (Caused by
>>> ConnectTimeoutError(<urllib3.connection.VerifiedHTTPSConnection object
>>> at 0x7fb8ed6901d0>, u'Connection to <Linux server IP> timed out. (connect
>>> timeout=30)'))
>>>
>>> 54.227.79.55 | FAILED! => {
>>>     "msg": "Unexpected failure during module execution.",
>>>     "stdout": ""
>>> }
>>>
>>> Don't know which protocol it uses to connect to the Linux server but I
>>> assume it is not ssh.
>>>
>>> Thanks
>>> Gil
>>>
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